“Instant Methylide” Modification of the Corey–Chaykovsky Cyclopropanation Reaction

Abstract

Treatment of various electron‐deficient alkenes in DMSO with stable, dry, equimolar mixtures of either Me₃S(O)I/KOt‐Bu or Me₃S(O)I/NaH cleanly afforded the corresponding substituted cyclopropanes in good yields and short reaction times (<20 min for reactions at 50–60°C using 0.4–4.0 mmol alkene).

Keywords:

• Corey–Chaykovsky reactions
• cyclopropanation
• methylide
• MIRC reaction

Acknowledgments

We are grateful for the generous financial support provided by the Fordham University Clare Boothe Luce Undergraduate Scholars Program (support for C. E. A.), Research Corporation Cottrell College Science Award No. C‐3698, and the National Science Foundation's Division of Undergraduate Education through Grant DUE #9650684.